253 Jefferson St, Winchester, VA 22601
Property image
Property image
OFF MARKET

$548,300

Trulia Estimate
  • 3 Beds
  • 1.5 Baths
  • 2,100 sqft

253 Jefferson St, Winchester, VA 22601

Est. Refi. Payment $3,174/mo*
Refinance Your Home
Currently Off Market - Sold Sep 20, 2024 for $510,000

Home Value

Trulia Estimate
$548K
Since last month
Decreased$2K (-0.4%)
Since last year
Increased$26K (+5%)
Since last sale
Increased$38K (+7.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +72% in the last 10 years
MonthEstimated value
2026
August 2026$548K
August 2026$548K
July 2026$550K
June 2026$552K
May 2026$551K
April 2026$538K
March 2026$531K
February 2026$526K
January 2026$526K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
257 Jefferson St, Winchester, VA
0.01
Single-Family Home
$500,000
09/12/25
3
2
2,285
236 Miller St, Winchester, VA
0.05
Single-Family Home
$465,000
02/20/26
3
2.5
1,978
237 Miller St, Winchester, VA
0.07
Single-Family Home
$449,900
09/23/25
3
2
1,293
431 Jefferson St, Winchester, VA
0.27
Single-Family Home
$425,000
03/11/26
3
1.5
1,632
154 Montague Ave, Winchester, VA
0.20
Single-Family Home
$449,000
03/27/26
3
1.5
2,303
407 Jefferson St, Winchester, VA
0.21
Single-Family Home
$464,000
04/13/26
3
2
2,805
436 W Leicester St, Winchester, VA
0.41
Single-Family Home
$500,000
10/15/25
3
1.5
1,592
227 Miller St, Winchester, VA
0.07
Single-Family Home
$475,000
03/27/26
3
4
3,359
31 W Whitlock Ave, Winchester, VA
0.26
Single-Family Home
$380,000
03/13/26
3
1.5
1,416

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
257 Jefferson St, Winchester, VA 22601
0.01
$511,400
3
2
2,285
Off Market
308 Miller St, Winchester, VA 22601
0.04
$445,300
3
2
1,815
Off Market
236 Miller St, Winchester, VA 22601
0.05
$465,000
3
2.5
1,978
Recently Sold
332 Miller St, Winchester, VA 22601
0.10
$336,300
3
2
1,611
Off Market
336 Miller St, Winchester, VA 22601
0.11
$537,900
3
2.5
1,865
Off Market
237 Miller St, Winchester, VA 22601
0.07
$460,000
3
2
1,293
Off Market
227 Miller St, Winchester, VA 22601
0.07
$475,000
3
4
3,359
Recently Sold
312-314 E Piccadilly St, Winchester, VA 22601
0.09
$409,600
6
-
1,260
Off Market
219 Jefferson St, Winchester, VA 22601
0.09
$572,400
5
4
3,616
Off Market
1207 Valley Ave, Winchester, VA 22601
0.10
$558,300
4
2.5
2,544
Off Market
356 Miller St, Winchester, VA 22601
0.15
$421,000
6
2
1,915
Off Market

Local Information

  • Map ViewExplore the area around 253 Jefferson St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1955
2,100 sqft
$261/sqft
Open Parking

About this House

This gem in the historical Handley area of Winchester has amazing views of the John Handley High School campus. John Handley High is registered on the National Register of Historic Places, and has a rich history as a privately endowed public school. The side to side front porch overlooks the campus and is across from a grove of historical cherry trees with colorful pink blooms every spring. Stroll over to the walking paths surrounding the campus or enter the trails to the Museum of the Shenandoah Valley at the end of the street. The location of this home is located adjacent to the parade route for the Apple Blossom Festival bringing thousands of spectators to the town each May. The front porch is perfect to watch the 10 K race and with front row seats to watch the annual fireworks as part of the festival. Also it is located within walking distance to the Old Town Walking Mall to enjoy local restaurants, boutiques, museums and more! 253 Jefferson has had only 2 owners since it was built. There have been many mechanical improvements throughout the years leaving the updating and cosmetics to your liking. The backyard is fenced on 2 sides, has a nice shed & all brick covered patio for outdoor entertaining. Come see for yourself the neighborhood and all it's amenities surrounding this all brick, solid bones home!
253 Jefferson St, Winchester, VA 22601 is a 3 bedroom, 2 bathroom, 2,100 sqft single-family home built in 1955. It last sold for $510,000 on Sep 20, 2024 (2% above the $499,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $548,300, with a rent estimate of $2,134/month.
Last check for updates: about 19 hours ago
Listed by Cynthia Butler, (540) 533-6969
Long & Foster Real Estate, Inc.
Bought with: Cynthia Butler, (540) 533-6969, Long & Foster Real Estate, Inc.
Source: Bright MLS, MLS#VAWI2006182

Home Details for 253 Jefferson St

Interior Features

Interior Details
Basement: Full,Interior Entry,Space For Rooms,UnfinishedNumber of Rooms: 9Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 2100 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Cable, Other Internet ServiceAppliances: Microwave, Dishwasher, Self Cleaning Oven, Oven/Range - Electric, Refrigerator, Stainless Steel Appliance(s), Cooktop, Washer, Dryer, Electric Water HeaterDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Other,OilHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Oil
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Flooring: Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Hardwood, Wood
View
Has a ViewView: Panoramic, Other, Trees/Woods, Park/Greenbelt, Garden

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Brick, Porch, Patio, RoofOther Structures: Above Grade, OutbuildingExterior: Rain Gutters, SidewalksFoundation: BlockNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Off Street,On Street
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2100 Square Feet

Property Information

Year Built
Year Built: 1955Year Renovated: 2011
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: BrickNot a New Construction
Property Information
Condition: ExcellentParcel Number: 21204F 3

Price & Status

Price
List Price: $499,000
Status Change & Dates
Off Market Date: Tue Sep 24 2024Possession Timing: Immediate

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: WINCHESTERCommunity: Downtown Winchester
School Information
Elementary School: John KerrElementary School District: Winchester City Public SchoolsJr High / Middle School: Daniel MorganJr High / Middle School District: Winchester City Public SchoolsHigh School: John HandleyHigh School District: Winchester City Public Schools

Building

Building Area
Building Area: 3150 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 6055 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAWI2006182Above Grade Unfinished Area: 2100

Price and Tax history

DateEventPrice
Sep 20, 2024
Source: Bright MLS #VAWI2006182
Sold
$510,000
Aug 23, 2024
Source: Bright MLS #VAWI2006182
Contingent
$499,000
Aug 14, 2024
Source: Bright MLS #VAWI2006182
Listed For Sale
$499,000

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$393K
$3.33KMoM
Sale-to-List Price
99.9%
0.1%MoM
Price per sq ft
$221
$1MoM
Available listings
346
37MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winchester

At least 465 Trulia users voted on each feature.

  • 84 % Say car is needed

  • 81 % Say it's dog friendly

  • 81 % Say parking is easy

  • 77 % Say yards are well-kept

  • 73 % Say there's holiday spirit

  • 69 % Say kids play outside

  • 64 % Say people would walk alone at night

  • 64 % Say there are sidewalks

  • 59 % Say streets are well-lit

  • 55 % Say it's quiet

  • 52 % Say neighbors are friendly

  • 49 % Say it's walkable to restaurants

  • 49 % Say there's wildlife

  • 48 % Say they plan to stay for at least 5 years

  • 36 % Say it's walkable to grocery stores

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • 7seymours
    "It’s quiet, owners take care of their homes, and it’s safe! And pretty! "
    5
    Flag
  • Hmrtgptw2c
    "I drive to and from work. The city has public transportation with WinReady I think it’s called. There is ride share in the area as well."
    4
    Flag
  • George
    "I’ve only lived here several weeks but am impressed by the people in our neighborhood. Polite and friendly."
    11
    Flag
  • Jessica J Contreras
    "There are no sidewalks or safe areas to walk with pets. Cars go by fast. It would be unsafe to walk. "
    2
    Flag
  • 7seymours
    "We live in a beautiful, safe area with an excellent county school system. Our neighbors have pride and take care of their properties in the Green Spring area"
    10
    Flag
  • Izzy874
    "Apple blossom every single year I love it! The food is amazing, the games, the carnival, and especially the parades and events to go too!"
    4
    Flag
  • Singsongone
    "Lived in this quiet neighborhood little over ten years. Convenient to major highways and bypasses, hospital, doctors, grocery and retail stores, restaurants. Lovely mature trees throughout, some wildlife and one can easily hear morning/evening birds. Residents take pride in the appearance of their homes and yards and look out for one another. "
    5
    Flag
  • Smlrws
    "I’ve lived here for a year and my street is much quieter than I ever expected since I live with a mile of the downtown area. It’s safe. There are many restaurants, coffe shops, hair salons, etc. within walking distance !"
    6
    Flag
  • Kelrendon83
    "Great community for live , safe and good for raise kids and the family can have a good place to visit , some good festivals "
    12
    Flag
  • 7seymours
    "Lived here for 22 yrs. Beautiful, spacious, quiet and good neighbors! We feel safe here with a lot of privacy. Neighbors look out for each other & help each other "
    11
    Flag
  • Gfbzc98z9n
    "It is Quiet and safe while still being just a short trip to the big city. Beautiful downtown walking mall. Great outdoors all around in the Blue Ridge Mountains."
    9
    Flag
  • 7seymours
    "Apple Blossom Festival which is held annually with parades, celebrities, dances, music & arts & crafts. A beautiful weekend during Apple Blossom time with over 250,000 visitors attending this special event in the Shenandoah Valley "
    10
    Flag
  • Trulia User
    "Everyone I have ran into has been nice. Definitely a very family friendly neighborhood. Feels very cozy "
    8
    Flag
  • Morganva
    "Dog friendly, plenty of green space, and lots of dog bag dispensers for cleaning up after the pooch. "
    8
    Flag
  • Bridgetdefoe
    "It’s easy to get around Winchester. Roads are well maintained. Traffic is minimal. You can get about anywhere in Winchester is less than 20 minutes. Rt 7 has become busy as an exception due to people commuting to Loudoun County "
    9
    Flag
  • Isabelle M.
    "Is a nice ride and no traffic in the area, many shopping centers, great area to visit, one of the great hospital in the nation."
    7
    Flag
  • Alliav11%40gmail.com
    "A lot of people have dogs here and they are always waking them. There are a lot of stray cats so if dogs don’t like them beware"
    0
    Flag
  • Gina A.
    "It's just a nice neighborhood to walk. People are always waving and stopping to chat. And they clean up after their dogs"
    4
    Flag
  • Cooda K.
    "It’s a lot It’s a lot I can say I honestly feel like it’s a beautiful place I mean the cabs suck But other than that I feel like it’s a nice expensive place to live 😁 "
    3
    Flag
  • Topeye
    "Very good schools, low crime rate, good jobs. Civic pride. Great long-running annual community festival. Many churches and civic organizations are active. Historic preservation. "
    5
    Flag
  • Rob R.
    "My commute to downtown is usually fairly quick, not too much traffic. Public transportation is not very popular."
    3
    Flag
  • Nickruiz270
    "The commute into Winchester is fairly light but around 5pm it’s when it gets heavy. I would try to avoid all small roads as much as possible and use the highway as much as possible. "
    2
    Flag
  • Careliza81
    "We are just walking distance to the walking mall which has tons of activities throughout the year. There are festivals for most major holidays and apple blossom. "
    3
    Flag
  • Nick A.
    "There is a great community of people here and it’s very welcoming. Living here is home for me and I would recommend moving here if you want to be close to major metropolis and still be near countryside"
    3
    Flag
  • Chels J.
    "Great safe place for kids no strange people more of a older group of people live here. It’s out of the way of the city but seconds from town"
    51
    Flag
  • Brock M.
    "Great area to live and raise a family. Good earnings potential. Great university. Awesome private and public school system."
    2
    Flag
  • Coach_ramos
    "You must drive or carpool. There is a local bus/trolley, but only locally within the city. No rail or subway."
    2
    Flag
  • Leslie H.
    "I commute to Northern Va and Loudoun Co. it’s more brutal each year, especially the return commute. "
    0
    Flag
  • Brad M.
    "Old town feel and downtown is lively. We enjoy being able to walk in a safe environment and walk to restaurants and shops. A great place to live in a historic town. "
    2
    Flag
  • Yesenia R.
    "The community center provides events for all. From all the holidays to special events for fundraisers along with also assisting the community with school supplies. There’s also playgrounds and pools."
    2
    Flag
  • Danielle M.
    "There are no community events in my neighborhood...everyone mostly keeps to themselves with the exception of those of us who have lived here for over thirty years. "
    0
    Flag
  • Erin G. .
    "Nothing special, just a nice neighborhood. Nice and quiet. Friendly folks. Safe for kids to play. Convenient to shopping."
    1
    Flag
  • Samantha F.
    "There is a large park just a few blocks away. Enough room to let a we trained dog off the leash. Walking distance to downtown dog friendly restaurants. "
    0
    Flag
  • Topeye
    "The public library across the street and the pedestrian mall 2 blocks away frequently hold community events."
    1
    Flag
  • Juanita e
    "dog owners would love this area great place to live great county sitting quite schools stores dr.s hospital close malls shopping casinos horse racing car raises movies drive in s close tons restaurants parks city county parks swimming snow skiing within hour"
    0
    Flag
  • Andrea
    "Nothing. Nice area not much for kid s to do no playgrounds or nearby parks but nice for adults "
    0
    Flag
  • Destiny W.
    "There's a big Park perfect for taking your dog. Plus you'll see all kinds of dogs being walked downtown on the waking mall. A few businesses even put a water bowl out for the dogs that walk by"
    2
    Flag
  • Debra T.
    "There is a bus stop only a few minutes from my front door. I know you can take the bus down town! I am not sure about long distance travel!"
    1
    Flag
  • Island4tj
    "The city is relatively safe and the schools are very good. Nice, clean town to live in that’s family-oriented. "
    1
    Flag
  • Ruizy8329
    "The neighborhood provides many sidewalks and grassy areas for peaceful and well lit dog walking. People in the area mostly have pets and those who don’t are usually very good about it. "
    1
    Flag

LGBTQ Local Legal Protections

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 253 Jefferson St

  • What is 253 Jefferson St estimated to be worth?
    Trulia's estimated value for 253 Jefferson St in Winchester, VA is $548,300.
  • What is the price history for 253 Jefferson St?
    253 Jefferson St in Winchester, VA last sold for $510,000 in September 2024.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $393K. That is up $3.33K from the prior month.
  • Does 253 Jefferson St have air conditioning?
    Yes, 253 Jefferson St in Winchester, VA has air conditioning.
  • Does 253 Jefferson St have laundry facilities?
    Yes, 253 Jefferson St in Winchester, VA has in-unit laundry.

Explore by feature - Pet Friendly

59 pet-friendly rentals in Winchester, VA

Explore by feature - Garage

31 rentals with a garage in Winchester, VA

Explore by feature - Air Conditioning

108 rentals with air conditioning in Winchester, VA

Explore by feature - Pool

16 rentals with a pool in Winchester, VA

Explore by feature - Washer/dryer

81 rentals with a washer/dryer in Winchester, VA

Explore by feature - Outdoor Space

17 rentals with an outdoor space in Winchester, VA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 253 Jefferson St

Skip to last item
Skip to first item

Homes for sale near 253 Jefferson St

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item